7-ketocampesterol | 103616-84-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 7-ketocampesterol
• 英文别名: (1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R)-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,6H,7H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-4-one；(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5,6-dimethylheptan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 103616-84-8
• 化学式: C₂₈H₄₆O₂
• 分子量: 414.672
• InChiKey: LTLKHSBYMNKWPF-UYGIXTBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-ketocampesterol 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 生成 7β-hydroxycampesterol
  参考文献：
  名称：

  Synthesis and assessment of the relative toxicity of the oxidised derivatives of campesterol and dihydrobrassicasterol in U937 and HepG2 cells

  摘要：

  The cytotoxic effects of the oxidised derivatives of the phytosterols, stigmasterol and beta-sitosterol, have previously been shown to be similar but less potent than those of the equivalent cholesterol oxides in the U937 cell line. The objective of the present study was to compare the cytotoxic effects of the oxidised derivatives of synthetic mixtures of campesterol and dihydrobrassicasterol in both the U937 and HepG2 cell lines. The parent compounds consisted of a campesterol: dihydrobrassicasterol mix at a ratio of 2:1 (2CMP:1DHB) and a dihydrobrassicasterol:campesterol mix at a ratio of 3:1 (3DHB:1CMP). The 2CMP:1DBH oxides were more cytotoxic in the U937 cells than the 3DBH:1CMP oxides but the difference in cytotoxicity was less marked in the HepG2 cells. The order of toxicity of the individual oxidation products was found to be similar to that previously observed for cholesterol, beta-sitosterol and stigmasterol oxidation products in the U937 cell line. There was an increase in apoptotic nuclei in U937 cells incubated with the 7-keto and 7 beta-OH derivatives of both 2CMP:1DHB and 3DHB:1CMP and also in the presence of 3DHB:1CMP-3 beta,5 alpha,6 beta-triol and 2CMP:1DHB-513,613-epoxide. An additional oxidation product synthesised from 2CMP:1DHB, 5,6,22,23-diepoxycampestane, was cytotoxic but did not induce apoptosis. These results signify the importance of campesterol oxides in the overall paradigm of phytosterol oxide cytotoxicity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2012.04.019
• 作为产物：
  描述：

  在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 7-ketocampesterol
  参考文献：
  名称：

  Synthesis and assessment of the relative toxicity of the oxidised derivatives of campesterol and dihydrobrassicasterol in U937 and HepG2 cells

  摘要：

  The cytotoxic effects of the oxidised derivatives of the phytosterols, stigmasterol and beta-sitosterol, have previously been shown to be similar but less potent than those of the equivalent cholesterol oxides in the U937 cell line. The objective of the present study was to compare the cytotoxic effects of the oxidised derivatives of synthetic mixtures of campesterol and dihydrobrassicasterol in both the U937 and HepG2 cell lines. The parent compounds consisted of a campesterol: dihydrobrassicasterol mix at a ratio of 2:1 (2CMP:1DHB) and a dihydrobrassicasterol:campesterol mix at a ratio of 3:1 (3DHB:1CMP). The 2CMP:1DBH oxides were more cytotoxic in the U937 cells than the 3DBH:1CMP oxides but the difference in cytotoxicity was less marked in the HepG2 cells. The order of toxicity of the individual oxidation products was found to be similar to that previously observed for cholesterol, beta-sitosterol and stigmasterol oxidation products in the U937 cell line. There was an increase in apoptotic nuclei in U937 cells incubated with the 7-keto and 7 beta-OH derivatives of both 2CMP:1DHB and 3DHB:1CMP and also in the presence of 3DHB:1CMP-3 beta,5 alpha,6 beta-triol and 2CMP:1DHB-513,613-epoxide. An additional oxidation product synthesised from 2CMP:1DHB, 5,6,22,23-diepoxycampestane, was cytotoxic but did not induce apoptosis. These results signify the importance of campesterol oxides in the overall paradigm of phytosterol oxide cytotoxicity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2012.04.019